• Title/Summary/Keyword: 3,5-di-O-caffeoylquinic acid

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Five Di-caffeoylquinic Acid Derivatives and a Coumarin from the Hot-water Extract of Artemisia annua (개똥쑥(Artemisia annua) 열탕추출물의 Di-caffeoylquinic Acid 및 Coumarin 성분)

  • Rho, Taewoong;Park, Chanyoung;Kim, Seon-Hee;Yoon, Kee Dong
    • Korean Journal of Pharmacognosy
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    • v.49 no.3
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    • pp.219-224
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    • 2018
  • Artemisia annua L. (Compositae) is an annual herb, which has been traditionally used as an antipyretic and hemostatic agent with the herbal medicine name of Cheong Ho (菁蒿) in Korea and China. In this study, five di-caffeoylquinic acid derivatives and a coumarin were determined from the hot-water extract of aerial parts of A. annua. The structures of isolates were elucidated to be 1,3-di-O-caffeoylqunic acid (1), 3,4-di-O-caffeoylquinic acid (2), 3,5-di-O-caffeoylqiunic acid (3), 1,5-di-O-caffeoylquinic acid (4) and 4,5-di-O-caffeoylquinic acid (5) and scopoletin (6). The presence of 1,5-di-O-caffeoylquinic acid (4) is firstly reported from A. annua in the current study.

The Inhibitory Effect of the Caffeoylquinic acid-Rich Extract of Ligularia stenocephala Leaves on Obesity in the High Fat Diet-Induced Rat

  • Nugroho, Agung;Bachri, Moch Saiful;Choi, Jong-Won;Choi, Jae-Sue;Kim, Won-Bae;Lee, Byung-Il;Kim, Jong-Dai;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.16 no.2
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    • pp.80-87
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    • 2010
  • High performance liquid chromatography (HPLC) analysis on the MeOH extract of Ligularia stenocephala leaves identified six caffeoylquinic acids, viz. 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoyl-mucoquinic acid, 3,5-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, and 3-Ocaffeoylquinic acid using standard compounds, and determined the quantity of each extract. Percentage of total caffeoylquinic acids of the MeOH extract and its BuOH fraction were calculated as $67.83{\pm}3.79%$ and $94.52{\pm}1.84%$, respectively. Since the caffeoylquinic acid-rich MeOH extract exhibited a potent peroxynitrite-scavenging effect in vitro ($IC_{50}=0.87{\pm}0.33\;{\mu}g/ml$ (mean $\pm$ SEM)), the experiment was designed to identify whether or not that extract has an anti-obesity effect on rat obesity induced by high fat diet. Oral administration of the MeOH extract and its BuOH fraction abundant in caffeoylquinic acid decreased the rat body weight to the level of untreated group and decreased abdominal fat pad weight. The atherogenic index and thiobarbituric acid-reactive substance (TBARS) values were restored by treatment, indicating that the caffeoylquinic acid-rich extract probably inhibited hyperlipidemia and oxidative stress caused by high fat diet. These results suggest that L. stenocephala in vegetable form or its caffeoylquinic acid-rich fraction (BuOH fraction) as an agent can be used for treatment or prevention of obesity.

HPLC Analysis on the Cafffeoylquinic Acids of Aster altaicus var. uchiyamae Kitamura and Peroxynitrite-scavenging Effect (단양쑥부쟁이에 함유된 Caffeoylquinic Acid의 HPLC 분석과 Peroxynitrite 소거효과)

  • Lim, Sang-Cheol;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.29 no.1
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    • pp.20-25
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    • 2016
  • Five caffeoylquinic acids of Aster altaicus var. uchiyamae Kitamura (Compositae) leaves were identified using standard compounds by HPLC and determined as follows: 3,4-di-O-caffeoylquinic acid (4.92 ± 0.06 ㎎/g dried weight), 3,5-di-O-caffeoylquinic acid (3.95 ± 0.13 ㎎/g), 4,5-di-O-caffeoylquinic acid (1.39 ± 0.10 ㎎/g), 5-O-caffeoylquinic acid (chlorogenic acid, 8.05 ± 0.21 ㎎/g), 3-O-caffeoylquinic acid (4.97 ± 0.18 ㎎/g). The total content of five caffeoylquinic acids were calculated as 26.73 ± 0.26 ㎎/g dried weight while the percentage of the five compounds in the MeOH extract was calculated as 25.22 ± 0.25%. The IC50 value of the MeOH extract scavenging peroxynitrite (ONOO) was shown as 5.16 ± 0.15 ㎍/㎖.

HPLC Analysis of Caffeoylquinic Acids in the Extract of Cacalia firma and Peroxynitrite Scavenging Effect (병풍쌈 추출물의 Caffeoylquinic Acid 성분 분석과 Peroxynitrite 소거효과)

  • Park, Hee-Juhn;Nugroho, Agung;Lee, Jin-Ha;Kim, Jong-Dae;Kim, Won-Bae;Lee, Kang-Ro;Choi, Jae-Sue
    • Korean Journal of Pharmacognosy
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    • v.40 no.4
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    • pp.365-369
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    • 2009
  • Six caffeoylquinic acids of Cacalia firma (Komarov) Nakai (Compositae) leaves were identified using standard compounds by HPLC. Each content of those compounds in dried weight was determined as follows: 3,4-di-O-caffeoylquinic acid (1.44${\pm}$0.04 mg/g of dried weight), 3,5-di-O-caffeoyl-muce-quinic acid (2.47${\pm}$0.12 mg/g), 3,5-di-O-caffeoylquinic acid (3.74${\pm}$0.24 mg/g), 5-caffeoylquinic acid (chlorogenic acid, 5.20${\pm}$0.09 mg/g), 3-caffeoylquinic acid (1.35${\pm}$0.01 mg/g) and 3-Op-coumaroylquinic acid (3.84${\pm}$0.25 mg/g). The total content of six caffeoylquinic acids in the plant material was calculated as 18.05${\pm}$0.69 mg/g while the percentage of the six compounds in the MeOH extract was calculated as 30.85${\pm}$1.18%. The $IC_{50}$ value of the MeOH extract scavenging peroxynitrite ($ONOO^-$) was shown as 3.22${\pm}$0.57 ${\mu}g$/ml.

Antioxidant Activities of Phenolic Derivatives from Dipsacus asper Wall. (II)

  • Hung, Tran Manh;Thuong, Phuong Thien;Youn, Ui-Joung;Zhang, Xin Feng;Min, Byung-Sun;Woo, Mi-Hee;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.2
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    • pp.107-112
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    • 2008
  • The six phenolic compounds isolated from the root of Dipsacus asper, 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4-5-di-O-caffeoylquinic acid (5), methyl 4,5-di-O-caffeoyl quinate (6) were continuously evaluated for their antioxidant activity using superoxide radical scavenging and AAPH-mediated (LDL) oxidation assay. The results demonstrated that compounds 1 - 6 had remarkable antioxidant activities with the $IC_50$ values ranging from 12.0 to $2.8{\mu}M$ in superoxide radical scavenging. They also inhibited AAPH-mediated low-density lipoprotein LDL oxidation by the generation of thiobarbituric acid reactive substances (TBARS) with $IC_50$ ranging from 6.7 to $8.7{\mu}M$.

Hepatoprotective effect of Ainsliaea acerifolia water extract on LPS/D-GalN-induced acute liver injury in human HepG2 cells (단풍취 열수 추출물의 HepG2 인간간세포의 LPS/D-Gal에 의해 유발된 급성 간 손상에 대한 간보호 효과)

  • Lee, Sun-Yeop;Han, Joon-Hee;Choi, Da-Hye;Hong, Min;Kwon, Tae-Hyung;Lee, Yong-Jin;Yu, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.52 no.5
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    • pp.476-481
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    • 2020
  • This study investigated the antioxidant and hepatoprotective effects of Ainsliaea acerifolia water extract (AAWE) on HepG2 cells. Five types of caffeoylquinic acid (CQA) were detected in AAWE, namely, 4,5-di-O-caffeoylquinic acid (4,5-DCQA; 11.16 mg/g), 3,4-di-O-caffeoylquinic acid (3,4-DCQA; 5.23 mg/g), 5-O-caffeoylquinic acid (5-CQA; 4.88 mg/g), 3,5-di-O-caffeoylquinic acid (3,5-DCQA; 3.51 mg/g), and 4-O-caffeoylquinic acid (4-CQA; 3.31 mg/g). AAWE exerted ABTS+ antioxidant effects, evidenced by polyphenol content and 2,2'2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH radical scavenging) activities. AAWE (300 ㎍/mL) treatment significantly decreased the activities of gamma glutamyl transferase (GGT), aspartate transaminase (AST), and lactate dehydrogenase (LDH) as compared to control and exerted protective effects against the increase in liver function index induced by lipopolysaccharide (LPS)/galactosamine (D-GalN) in HepG2 cells. In addition, the secretion of tumor necrosis factor (TNF)-α by HepG2 cells induced by LPS/D-GalN significantly increased in all treatment groups compared to that in the control. However, AAWE (100-300 ㎍/mL) treatment significantly decreased the secretion of TNF-α compared to that in the control. These results suggest that AAWE treatment reduces hepatotoxicity by increasing antioxidant activities, reducing GGT, AST, and LDH activities, and inhibiting TNF-α secretion.

Comparison of Phenolic Acid from Shoots of Aralia elata and Kalopanax pictus Cultivated in Korea Using UPLC-DAD-ESI(+)-QToF/MS (UPLC-DAD-ESI(+)-QToF/MS를 이용한 국내산 두릅나무 및 음나무 순 내 페놀산 특성 비교)

  • Kim, Young Jin;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Asamenew, Gelila;Lee, Suji;Lee, Sang Hoon;Cha, Youn-Soo;Kim, Jung Bong
    • Korean Journal of Environmental Agriculture
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    • v.37 no.4
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    • pp.260-267
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    • 2018
  • BACKGROUND: In this study, shoots of Aralia elata and Kalopanax pictus which belong to the Araliaceae family were analyzed using UPLC-DAD-ESI(+)-QToF/MS to characterize of individual phenolic acids. METHODS AND RESULTS: Total thirteen phenolic acids were identified, and nine hydroxycinnamic acid derivatives have been identified for the first time in shoots of Aralia elata and Kalopanax pictus. For total phenolic acid content (mg/100g dry weight), shoots of Aralia elata and Kalopanax pictus showed 754.8 and 845.3 mg/100g, respectively. 5-O-Caffeoylquinic acid (49%) and 3,5-di-O-caffeoylquinic acid (44%) were found as major phenolic acids in Aralia elata, while 5-O-caffeoylquinic acid (91%) was a major component in Kalopanax pictus. CONCLUSION: On comparing the two plants, it was considered that the biosynthesis of 3,5-di-O-caffeoylquinic acid can be affected by 5-O-caffeoylquinic acid in Aralia elata.

Pancreatic Lipase Inhibitors in the Roots of Taraxacum ohwianum, a Herb Used in Korean Traditional Medicine (민들레 뿌리로부터 Pancreatic lipase 저해 물질의 분리)

  • Kim, Tae-Wan;Kim, Tae-Hoon
    • Food Science and Preservation
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    • v.18 no.1
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    • pp.53-58
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    • 2011
  • Activity-guided isolation from an ethylacetate-soluble fraction of a 70% (v/v) ethanolic extract from the roots of Taraxacum ohwianum, using a pancreatic lipase inhibition assay, resulted in isolation and identification of five phenolic metabolites of previously known structure; these were 3,5-di-O-caffeoylquinic acid, chicoric acid, caffeic acid, protocatechuic aldehyde, and luteolin. All structures were confirmed by NMR and MS scpectroscopic data. Of these compounds 3,5-di-O-caffeoylquinic acid exhibited the most potent inhibitory activity, with $IC_{50}$ of $65.1{\pm}0.7\;{\mu}M$ against pancreatic lipase.

Development and Validation of HPLC-PDA Method and Pattern Recognition Analyses Using Eight Marker Compounds for the Quality Control Between the Seeds of Cuscuta chinensis Lam. and Cuscuta japonica Choisy

  • Nguyen, Duc Hung;Zhao, Bing Tian;Le, Duc Dat;Ma, Eun Sook;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
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    • v.25 no.4
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    • pp.334-340
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    • 2019
  • Cuscuta chinensis Lam. and Cuscuta japonica Choisy are parasitic plants. C. chinensis seeds were traditionally used for treatment of kidney and liver deficiencies. C. japonica seeds were used as tonic medicine to improve liver function and strengthen kidneys, treatment of high blood pressure, chronic diarrhea, and sore eyes. Cuscutae Semen are seeds of only C. chinensis in Korean Herbal Pharmacopoeia (K.H.P.). The developed HPLC-PDA method easily, accurately, and sensitively quantified using eight marker compounds [hyperoside (1), astragalin, (2), quercetin (3), kaempferol (4), chlorogenic acid (5), 3,4-di-O-caffeoylquinic acid (6), 1,5-di-O-caffeoylquinic acid (7), and 4,5-di-O-caffeoylquinic acid (8)]. In addition, the method may be used to distinguish seeds between C. chinensis Lam. and C. japonica Choisy. Furthermore, the result from the current study was applied to clarify samples between steam processed and unprocessed samples of C. chinensis by pattern analysis.

Qualitative Analysis of Phenolic Substances in Artemisia capillaris by LC-MS (LC-MS에 의한 사철쑥에 존재하는 페놀성 화합물의 정성분석)

  • Nugroho, Agung;Lim, Sang-Cheol;Park, Hee-Juhn
    • Korean Journal of Pharmacognosy
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    • v.43 no.4
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    • pp.302-307
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    • 2012
  • The herb of Artemisia capillaris in Chinese medicine is used to treat hepatic diseases. In this research, qualitative analysis was performed using a UPLC/Q-TOF-ESI-MS/MS method for rapid identification of phenolic substances from A. capillaris: three caffeoylquinic acids (chlorogenic acid, 3,5-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid), three flavonoids (hyperoside, isorhamnetin 3-O-robinobioside and quercetin) and three prenylated coumarins (6,8-diprenylumbelliferone, cedrelopsin and osthol) were identified. The three prenylated coumarins have not been reported from A. capillaris.